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  • Nick Myles

Handling Difficult Conversations

Difficult conversations in the workplace can be tricky, whether you are initiating the conversation or on the receiving end. Surprisingly often, people allow unacceptable work or behaviour because they’d rather avoid taking about it. In the long-run, not having the conversation makes it worse for everyone involved.

Mindset. The first thing to do when preparing for a difficult conversation is to stop labelling it difficult - if you’ve decided it’s going to be that way, it probably will. Instead try seeing it as an opportunity: what positive change can come from having this conversation? You might have to give someone negative feedback but how about viewing the conversation as a chance for them to improve and for you to support in this? Often with important conversations, in and outside of work, we make up our minds beforehand. Maybe because you think you’re right or you’ve assumed something about the situation/the other person. This mindset means you don’t really give the other person a fair chance, you’re not open to hearing their perspective. Approach a conversation with an open mind and be prepared to learn something new. You can do this by trying to step into their shoes, thinking about what they want from the conversation and why. Try this: An exercise we often use in workshops on Handling Difficult Conversations is to start a discussion in pairs on a subject that matters to both people, A is for the subject and B is against. Half-way through the discussion, we ask partners to swap sides so B is now debating against the subject. Give it a go, it can be quite an eye-opening exercise: it’s difficult to not just see someone else perspective but to really get behind it. Win-Win. A surefire way to make a conversation difficult is by going in to fight for what you want. Having this combat mentality might mean you win (this time) but it also means someone will lose and in the long-run, that's not good. Focus on how both parties can leave happy. Not only will you both stand to gain something but it’ll strengthen your working relationship. At Different Duck, we’re all about developing skills and confidence through practice. Successfully handling important conversations gets easier with experience and role-play is a great tool to improve these skills and overcome obstacles in a safe environment. However, if you have an important conversation coming up - there is little benefit in rehearsing for it. Practice your conversation skills in general but over-preparing for a specific conversation will only throw you off-guard when your counterpart doesn’t respond in the way you expected. Instead, know your opening line, know the facts and then be present to listen. Often, the hardest part of a conversation is getting it started, so knowing how you will open the conversation will set you off on a good foot. Even better, use the following format: - Explain what the conversation is about - Describe why it needs to happen - Ask them an open question To summarise the three things you should prepare for any important conversation: 1. The outcome: Know the purpose of the conversation and what the ideal outcome is. 2. The landmines: Think of any potential landmines to avoid or approach with caution - any sensitive subjects or potentially emotional areas (it’s also good to know your own) 3. The assumptions: Ask yourself if you’re approaching this with an open mind or if you’ve made assumptions about the other person or their intentions. Also think about what assumptions they may have made.

Our drama based workshops give participants the opportunity to put theory into practice and gain confidence in overcoming obstacles through experience. For more info on our experiential approach to training, visit

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